First Date
by xephwrites
Summary: Dean takes Samantha on their first date. WARNINGS: cross-dressing, feminized Sam, wincest, Sam is 16, graphic sex. This follows Becoming Samantha.


Sam woke slowly, smiling to himself. He was nestled against Dean, who was snuffing slightly into Sam's dark brown hair. Sam sighed and burrowed closer into his brother. Dean tightened his arms around Sam.

"Morning." Dean mumbled into Sam's hair.

"Good morning." Sam replied contentedly. "It's Saturday." He said. Dean made an acknowledging noise. "That means we get the next two days together." Dean repeated the noise. "Dean!" Sam whined. Dean chuckled.

"I know." He placed a kiss on Sam's forehead. "I'm happy about it." Dean paused for a moment. "Want to go out for breakfast?" Sam looked at him, eyebrows raised.

"Drive thru or sit down?" Sam asked hesitantly.

"Sit down. I want to take my girl out for breakfast." Dean said, nuzzling Sam's hair.

Sam's stomach flipped a bit. Dean wanted to go out, and he wanted Sam to dress. Sam had never left the privacy of their motel rooms dressed up before.

"What if people talk?" Sam said nervously. "What if they laugh at me?" Dean held Sam tight.

"If they do, I'll kick their ass." He said. Sam sighed. "Seriously, if people talk, let them. If they think it's wrong, they can go to hell. All that matters is that we're together, and we're happy, okay?" Sam nodded against Dean's chest.

Sam pulled away from Dean to find the black duffel that they bought for Sam's other clothes. It had been easy to sneak it past Dad. Dad didn't notice one more bag added to the pile, just like he didn't notice a lot of things with his sons. Thankfully he was on a hunt with Caleb and would be gone until the end of next week.

Sam opened the bag carefully, and Dean leaned over. Sam began pulling items out and lying them on the bed. They had collected a nice assortment of shirts, blouses and skirts for Sam, as well as a few bra and panty sets. They were only able to find one pair of shoes, and they were a pair of patent leather Mary Jane's.

Dean ran his hands over the different items as Sam arranged them. Dean's hand rested on a white button up blouse that had small white flowers embroidered on it. Sam smiled as he picked that up from the bed and placed it on the unused bed. He dug out a plain white bra. Dean was smiling to himself as he toyed with the hem of an ankle length blue skirt that had small flowers printed on it. Sam nodded and placed it on the other bed with the blouse.

Dean was picking through the bag and held up a pair of plain blue cotton panties that had a lace top. Sam suppressed a giggle as he took them from Dean. They both began carefully folding the clothes and repacking the black duffel.

Sam pulled down his pajama bottoms and tossed them onto his regular duffel. He was about to step into the panties when Dean stopped him.

"Let me." Dean whispered. Sam handed out the panties as Dean slid off the bed. He knelt on the floor at Sam's feet and held the panties out. Sam rested a hand on Dean's shoulder as she stepped into them. She flushed a bit as Dean slid them up her legs. Sam's cock gave an interested twitch and they both chuckled. Panties in place, Dean gave Sam's cock a quick rub, making her moan. Dean sat on the bed, reaching for his own duffel.

"Just wanted to do that." He said as he began pulling out his own clothes. They got dressed in silence. Dean did up the hooks on Sam's bra, as she was still having difficulties doing it blindly. Sam took a small makeup bag into the bathroom with her as Dean pulled on a flannel shirt over his t-shirt.

Samantha exited the bathroom, lips shining pink and her hair held back by a tiny silvertone hair band. Dean could see the nervousness in her eyes. He held his arms open and she walked into the embrace.

"Its okay, Samantha." He whispered. "You'll be fine, and I'll be with you the whole time." He kissed her temple, then the tiny mole beside her nose. Samantha scrunched her nose playfully as he pulled away. Dean's arm slid around her waist.

"Ready to face the world, Samantha?" He asked. She nodded and Dean swung open the motel door.

It was a bright, clear morning. The Impala reflected the sun beautifully. Dean walked to the passenger side and opened the door for her. She bit her lip and slid into the car. Once seated, Dean closed the door and made his way to the driver's side. Starting the car, Dean noticed that Samantha had her legs crossed at the ankle. Her hand reached out to rest on his knee as he pulled out of the parking lot. Dean left one hand on the wheel as he took her hand and squeezed.

They found a quiet diner, far enough away from the center of town that they shouldn't run into anyone who may recognize them. Dean held the door to the diner open for Sam and she stepped in shyly. The waitress looked up at them and waved. Samantha picked a booth and slid in, Dean sitting on the other side.

Dean could see how nervous she was. His hand came across the table and held hers. He gave a reassuring squeeze and winked at her. She smiled and squeezed his hand back.

"Good morning!" The waitress said in a cheerful voice. She placed menus in front of both of them. "What can I get you to drink?"

"Coffee, please." Dean said, opening the menu. The waitress turned to Sam.

"Orange juice please." Sam said, keeping her voice as soft as possible. The waitress nodded and walked away. Dean watched as the tension left Samantha's shoulders.

"Not that hard, is it?" Dean asked, keeping his voice lowered. Dean ran his thumb over her knuckles. Samantha looked up and held Dean's gaze. She was smiling.

"It's not." She said back. She looked around the diner, taking in everyone going about their own business. "No one cares." She looked back at Dean and smiled brightly. Dean picked up her hand and kissed her knuckles.

"I care, and that's all that matters." He said, his lips brushing her skin.

The waitress came back to the table with their drinks, with a huge smile.

"Have you decided what you're getting?" She asked, looking expectantly between them. Dean nodded towards Sam.

"I'll have the blueberry Belgian waffle, please." She said, handing the menu back. The waitress looked at Dean.

"I'll have the same." He said, handing back his menu. The waitress looked between them.

"You two are such an adorable couple." The waitress said before heading to the kitchen. Samantha's smile got brighter.

"See, Sammy." Dean said, taking her hand in both of his. "I told you everything would be fine." Samantha tucked her feet in between Dean's. Dean placed small kisses on every knuckle.

They sat in comfortable silence, holding hands and watching the world go by out of the large window. Sam was near bursting with excitement that no one passed comment or judgment.

The waitress arrived with their waffles, smiling brightly at them. They thanked her and dug in. Sam giggled at Dean, who had a chunk of blueberry hanging off his chin. He retaliated by wadding up one of the paper napkins and threw it at her.

After they paid and left a nice tip for the waitress, they left the diner hand in hand. Dean opened the passenger door again for Samantha. Once they were both settled in the Impala, Dean squeezed her knee.

"Where do you want to go?" He asked with a blinding smile. Sam shrugged. "We're on a date. Where do you want to go?" Sam blushed and looked down.

"A date?" She asked. Dean nodded and pulled out of the diner parking lot. "I just want to spend the day together."

Dean drove to the outskirts of the town. Sam was paying attention to every turn he took, just in case they got lost. Dean turned down a small dirt road almost hidden from view by trees. He carefully maneuvered the Impala around rocks and divots in the ground.

They reached a clearing and Dean parked the car. Samantha got out of the car and saw the small creek. Dean popped the trunk and pulled out a blanket. Samantha turned to Dean with a huge smile.

"You planned this." She said. Dean smirked and took her hand.

"And why do you think that I had this planned?" He asked teasingly. Sam shook her head and let Dean lead her beside the creek. Dean spread the blanket and kneeled. He tugged her down with him.

Samantha lay on her back on the blanket. Dean rested on his side, his head propped on his arm. His free hand came out to play with a lock of her hair.

"This how you wanted to spend the day?" Dean asked softly. Sam closed her eyes and nodded. Dean touched her cheek with the back of his hand.

Dean leaned down and placed a soft kiss on her lips. Sam hummed and tried to follow Dean when he pulled away. Dean chuckled and kissed her again, this time brushing his tongue against the seam of her lips. She parted her lips and let her tongue touch his.

Slowly, they explored each other's mouths, their tongues almost dancing. Samantha wrapped her arms around Dean's neck and pulled him closer. Dean let the hand not supporting his weight trail along her side.

Dean broke the kiss and began trailing his lips along her jaw. Samantha sighed and ran her hands down his back. She pulled at his shirt, urging him on top of her. He shifted his weight, resting gently on her.

"Love you, Sammy." Dean whispered into her neck. He placed small kisses along the smooth skin. "So beautiful. I'm so lucky to have you." He leaned up and captured her lips once more. This time, their kiss was more heated, desperate almost. Samantha pulled at the hem of Dean's shirt.

"Off." She whispered against his lips. Dean pulled away long enough to pull the shirt over his head. Samantha sat up and took hers off as well, lying back on the blanket only in her bra. Dean took a moment to stare at her before leaning back down to kiss her collar bone. She pushed up into the touch.

Dean's fingers trailed along the delicate fabric around her ribs, quietly asking permission. When she didn't brush his hand away, he slipped his fingers under the wire to touch her nipple. She arched into the touch. Feeling a bit bolder, he pushed the bra up, exposing her nipples to the late morning sun. He gently took one into his mouth and teased it. Sam mewled and ran her hands through the dark blond spikes.

One hand dropped down to the waist of her skirt and danced along the sensitive skin of her stomach. Dean released the nipple and looked questioningly at her. She nodded and pushed the waistband of her skirt down. Carefully, Dean tugged the fabric down, revealing the small cotton panties. Sam's cock was hard and leaking, barely contained by the soft material.

Samantha was panting, her hips rolling, looking for contact. Dean cupped the erection, making Samantha moan. Dean placed small kisses along the lace trim of the panties, starting to tug them down off her hips.

Dean sat back on his heels to admire her for a moment. Her tongue peeked out of her mouth to wet her bottom lip. Her bronze skin was almost glowing in the sun. Her cock was fully hard and resting against the dark wiry hair. She reached out for Dean's jeans. He fished in the pocket for the lube he hid in there and placed it on the blanket. Samantha undid the button and pulled at the zipper. She reached in and touched his cock through his boxers, pulling a moan from him. Dean pushed his jeans and boxers past his hips and leaned forward. Samantha spread her legs and he lay between them.

Their cocks brushed together, making them both moan. Dean captured Samantha's lips in another heated kiss. He wriggled out of his jeans, kicking them into the grass beyond the blanket. Her hands slid down his back to rest on the round globes of his ass. She pushed down to bring them together again.

"Want you." She breathed against his mouth. Dean reached up and grabbed the container of lube.

"Anything for my girl." Dean breathed back. He gave her one last kiss before sitting back on his heels again and popped the cap on the container. He poured a generous amount onto his fingers before settling back over Samantha. He trailed his wet fingers around the base of her cock and down behind her balls. He pressed against the small hole lightly. She mewled and pushed against his fingers.

Dean eased a single finger inside, breaching the tight muscle. Sam sighed and pushed back against him, trying to get him in further. Dean crooked his finger, enjoying the silky heat around him, desperate to be buried inside her.

He gently added another finger, making Samantha gasp and buck. He spread his fingers, loosening the muscle. Dean pushed in harder, twisting his fingers. Samantha's body rose off the blanket as he hit her sweet spot. She cried out his name.

Carefully pulling his fingers out, he spread lube on his cock and lined up with her hole. She wrapped her legs around his waist, pulling him forward. His head nudged the hole and he slowly pushed forward. Inch by inch, he eased into her body. When he was fully seated, he gave her a languid kiss.

He thrust slowly, going as deep as he could inside her. Every thrust pulled a sound from one of them. Dean placed kisses all along the side of her neck. She scraped her nails lightly down his back. Sam was leaking precome between them as she rose to meet his hips.

"Love you." She gasped, tightening her legs around him. Dean's hips rocked faster.

"Love you too." He panted against her neck. A thin layer of sweat covered both of them as the sun rose to its highest point. He shifted his position and brushed her prostate. She keened and pushed back harder.

"More." She panted, kissing the side of Dean's face. He moved a bit faster, hitting the small bundle of nerves on every pass. His head came up and their lips met in a sloppy mess.

They got closer to orgasm with every frantic thrust, every brush of lips. Sam was starting to shake and keen loudly. Dean's movements became more erratic.

"Love you Samantha." Dean breathed. Her grip on his back tightened and her whole body seized.

"ohgodloveyoutoo." She screamed as ropes of milky white come landed between the two of them. The tightening of the muscles around him was more than enough to send Dean tumbling over the edge. He thrust as deep as he could into her, filling her.

They lay tangled in each other, catching their breaths. Samantha trailed her hand along Dean's arm. Dean peppered kisses along her cheekbone.

"You know I mean that, right?" Dean said softly. Samantha looked at him questioningly. "That I love you, and that I'll do anything for you." Samantha smiled and pulled him in close.

"Anything?" She asked.

"Anything." Dean said as he kissed her.


End file.
